Note: it's the guy who's reluctant in this story, so skip it if that's not what you're looking for!
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In my early 20's, I and a group of friends from school went to Las Vegas for a vacation on a shoestring budget. On the trip was my girlfriend, Jenn, a beautiful girl who was probably a little bit out of my league. She had long dark hair and brown eyes, a caring and sensitive personality, and an easy-going nature that puts you at ease. Plus, I knew that, under the loose-fitting shirts, she hid a spectacular pair of 34D breasts and large wine-colored areolas.
Our relationship was going well, although I admit I was a little underwhelmed by her sex drive. She was much more into massages and long kisses than getting down and dirty. Plus, I'm a night owl and she had a tendency to fall asleep early, so we would sometimes go long stretches without being intimate. All in all, though, I was happy with Jenn and could see us staying together for a long time.
Among the others on the trip was my ex-girlfriend, Emily, as well as her boyfriend, Josh. Emily was very different than Jenn. In some ways, calling her my ex isn't accurate, as she was more of an exclusive fuck-buddy for about a year. I could never get myself to fully commit to her as a girlfriend. Part of the reason was that she was
so
fun and
so
eager to get under the sheets, that I had a hard time seeing her as a serious partner. The other part--and I'll admit I am shallow here--was that I wasn't satisfied with her A-cup tits.
That said, I have to admit that Emily was really hot. Short, slim, and very pale with dark red hair in a bob cut that matched her neatly trimmed red landing strip. Her little breasts were topped with small, hard nipples that were bright pink like chewed bubble gum. What she lacked on top, however, she made up for with gorgeously bulging hips and a soft round ass.
And did I mention the eagerness? Emily is a girl who, with every lingering stare she and posture of her body, seemed to be constantly in heat. She knew how to tease me and make me forget everything else except getting into her pants.
The first time we fucked, she took an inch of me into her tight pussy and a devil's smile appeared on her lips.
"I think you're going to have to stretch me out a little," she told me, "Please don't be shy."
And she wasn't kidding, as I pushed into her, she had the tightest cunt I'd ever felt. Her insides wrapped around me, form-fitting, and massaged every inch of my member. It was like she had been molded specifically to pleasure me.
"I want you to finish first," she would say. "The feeling of hot cum shooting into me gets me off."
I was happy to oblige. It was the longest period of time in my life I went without masturbating because Emily was always there to relieve me, no questions asked. The sex kept me with her for so much longer than we should have been together. In retrospect, I think it was an addiction, because she was so hart to quit. In the end, though, I had to break it off because I hoped to actually settle down some day and Emily wasn't "the one."
Now a year later, I had fully kicked my Emily habit and was happy to be with Jenn. Jenn didn't really know too much about my history with Emily, as they weren't close, and I was happy to keep it that way.
You don't need a ton of money to have fun in Vegas, so the biggest expense we faced was the hotel for the weekend. Rather than tolerating a run-down dump, we stayed on the strip, but decided to save cash by sharing one double queen room. Two beds for eight people meant four to a bed, so Jenn and I ended up cramming into a bed with Emily and Josh.
And that's how I found myself trying to sleep between my girlfriend and my former fuck-buddy late one evening. The room was silent as I laid on my side, turned toward Jenn, with an arm around her. She quickly fell asleep, but I was not feeling particularly tired.
Trying not to make any noise, I started brushing my fingers over one of Jenn's nipples. It became hard and sensitive under my touch. She squirmed a little, indicating with body language that she was not interested. I understood her reluctance, it certainly wasn't the right time with so many people around.
Still, I couldn't help but feel a little aroused from my playing. I continued to lie there awake, wishing that it hadn't been over two weeks since we'd last had sex.
Deep in my lamentations, I hardly noticed that something was brushing up the back of my leg. A knee? No, too small... It's a finger. It traced it way up and over the front of my thigh, right into my boxer shorts, and suddenly a hand was cupping my balls.
It was Emily from behind me. I felt her fingers tighten around my testicles and then release. She ran a thin finger from the base of my cock up to the head. Being already half-aroused, my dick hardened almost immediately, pressing through the fly of my boxers, and I had to move back from Jenn to avoid poking her with it.
Now that I had pushed back into Emily, she wrapped a leg around my waist and started to slide up and down my body. I felt a long, slick, patch of wetness painting my outer thigh and my mind was instantly filled with visions of Emily's perfect pussy, pink and soft and always hungry for my cock.
Drips of precum started to form on my member and I had to turn to face Emily to avoid getting any on Jenn's ass. As I turned, some of my friends in the other bed moved and someone mumbled in their sleep. I stayed motionless not wanting anyone to wake up and find me like this.
Emily took advantage of the situation and grabbed my member with both hands. She skillfully stroked me up and down, gently touching my glans and using my precum as lubricant. "What is she doing?!" I thought. "I have to stop this!"
My body didn't seem to agree. Emily's firm grip and slow steady motion made me twitch and shake in the bed. Now Jenn was moving a little. Shit, was she going to wake up?
I pushed away from Emily and pressed my back against Jenn. Emily released me from her grasp, but when she did so, she also pulled my boxers down, quickly using her feet to completely remove them. I leaned forward to whisper directly into Emily's ear.
"Please stop this!" I hissed, trying desperately not to make a sound audible to others.
Emily took the opportunity to place two of her fingers into my mouth. A familiar sour taste followed. It was the taste of what flowed out of Emily's pussy when she was extremely turned on. Taste is memory, and the memories flooded back like the juice between her legs. I recalled Emily straddling my head and grinding her cunt on my mouth as she arched her back. With eyes closed and loud moans, she would bring herself repeatedly to orgasm while pinching the nipples of her small pale white tits, drenching my face in the process.
I was rock hard again. But I was able to pull her hand out of my mouth. She rotated to face her boyfriend. "Thank God it's over," I thought.
Jenn stirred again, this time changing positions in the sheets behind me. I froze. Then, on the tip of my erect cock, I felt Emily begin to wrap a hand around me again, very tightly this time. I must have been oozing a ton of precum because her fingers felt incredibly wet as she squeezed just the head of my aching stick. Unless that wetness was...no!
It wasn't until she had half engulfed me that I realized Emily wasn't using her fingers. She was pushing her luscious ass back towards me and claiming my shaft with her dripping pussy. Emily still fit me like a glove. She pressed into me forcefully until my whole length was taken into her body. The sensation of sliding into her tight supple folds made me instinctively thrust forward to meet her and the veins of my cock strained to fill every millimeter of her depths.